


Dare

by Inell



Series: Smutty McSmut Drabbles [4]
Category: Teen Wolf (TV)
Genre: Alternate Universe, Anal Play, Banter, Boss/Employee Relationship, Camboy Stiles Stilinski, Camboy Stiles Stilinski By Night, Derek Hale is Co-Owner of Stiles' Company, Exhibitionism, IT Tech Stiles Stilinski By Day, Knotting, Knotting Dildos, M/M, Masturbation, Mutual Pining, Oral Knotting, Secret Identity, Stiles Does Not Know Derek Is His Client, Stiles Stilinski Has a Big Dick, Talking, Versatile Derek Hale, Versatile Stiles Stilinski, Voyeurism, Werewolf Derek, kind of
Language: English
Status: Completed
Published: 2017-07-01
Updated: 2017-07-01
Packaged: 2018-11-21 23:44:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,260
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11368107
Author URL: https://archiveofourown.org/users/Inell/pseuds/Inell
Summary: Stiles performs a private show for a new client





	Dare

**Author's Note:**

> nothingtoseeherejustmovealong said: Prompt: Cam-boy Stiles, poly with Sterek end-game & marauders-mess said: First of all, I love the things you write, I really appreciate your talent

 

In the beginning, Stiles tried it out because he’d heard he could make some extra cash just getting off. After doing a lot of research, he decided to go for it. He’d been starting his sophomore year in college, and his extended course load hadn’t left time to work a traditional job. For the first month, he only had a few visitors to his room, and he only made a couple hundred dollars in tips. That was better than no money, though. Besides, he quickly realized that he got off being watched.

Over time, he started to get more attention, possibly because he’s into anal play and likes pushing his limits on camera but also maybe because he talks a lot. He never gives real personal information, but he does talk about other interests so long as they can’t be used to find his real name. He fantasy-talks, too, which seems to turn some of his visitors on. Enough that they come back and make requests when they eventually get the nerve.

Four years later, school is done, he’s working for a successful local company, Hale Enterprises, as an IT help desk tech, and he’s banking nearly seven grand a month on the side. It’s a really good number for a camboy, or so he’s been told. He has regulars that he recognizes by their screenname, has upgraded his computer system with the best cameras and software so he can listen to the messages he’s sent while performing a show, and he has turned his guest room into a filming studio so there’s no risk of anyone seeing something that could really identify him unless they already know him.

Of course, he’s got people who visit his room solely for conversation, but most of them are just in it for his ass or his dick. He does have a really nice ass, so he can understand that. As for his dick, it’s above average, and he doesn’t mind spending an hour fucking his fist or using a fleshlight if people want to pay to watch it. There are trolls sometimes, but not that many. His contract is solid, with more freedom than his original site had, and it’s like a part-time business doing something he enjoys that also happens to pay really well.

The thing is, he doesn’t even _need_ to keep performing, but he’s just really into the whole exhibitionism thing.

Since he does work full time, he usually schedules shows on Friday and Saturday nights, but he likes doing one in the middle of week to break up the monotony of his work week. That’s when he tends to schedule the private shows because he can pull in several hundred dollars if he caters to someone’s specific tastes, and they only take an hour or two. Perfect for a work night.

Tonight is one of those private shows; this time, it’s with a new client.

Lobo88 appeared in Stiles’ room about a month ago. On Saturday, he’d finally gotten in touch to set up a private show, offering to pay double what Stiles usually charges for two hours. It’s now Thursday, and Stiles is ready to give Lobo his money’s worth. After sending the private room log-in info, he waits for his new client.

It takes ten minutes before Lobo88 arrives in the room.

“Should I call you Lobo?” Stiles asks. People are often particular about what he calls them during private shows. He just hopes this isn’t another guy wanting to be called Daddy because that’s so not something he’s into in his personal life. Maybe being _called_ Daddy, not that he’s going to mix his personal life with his professional.

The computer speaks for Lobo. “You don’t need to call me anything.”

“Seriously?” Stiles arches a brow and looks into the camera. “Fine. I’ll call you baby. What do you want me to do for you tonight, baby?”

“You’re such a brat.” There’s a pause. “Did the package arrive?”

“What package?” Stiles waits a heartbeat before he reaches over the side of the bed, making sure to show off his ass to the camera, and he grabs the box that he picked up from the postal place on his way home. It had actually arrived Tuesday, but he knows his lack of patience, so he’d deliberately left it until today so he wouldn’t open it. “You mean this package? You know, when you wanted my PO Box, I didn’t realize I’d be receiving a present.”

“You’re not stupid, so don’t pretend that you are. You don’t have to play that game with me. Just be yourself, no pretending,” Lobo says, and Stiles sort of hates the fact that the guy is just watching and didn’t want to skype because he’d like to have heard that statement to know if he’s annoyed or joking. “Did you open it yet?”

“Nope. I wanted to wait to open it with you, baby.” Stiles winks at the camera and looks at the box, making a show of shaking it. “Are you ready for me to open it now?”

“I already said no to baby. Remember?” Lobo is pretty difficult considering he’s the one who approached Stiles for this show. “I’m ready. Open the box.”

“Bossy, aren’t you, dude?”

“Don’t call me dude.”

Stiles blinks, taken out of the act for a moment as he remembers hearing those exact words muttered by the illegally gorgeous CFO of his company during his first day working at Hale Enterprises. Great. Now he’s going to start thinking of Lobo as Derek Hale, which is just wrong on several different levels. The primary one being that Derek Hale is co-owner of Hale Enterprises, which makes him Stiles’ boss, and the secondary being that Derek Hale can’t stand him. He’s noticed the glares and frowns thrown his way the times their paths have crossed.

“You can call me Dare.”

“Huh?” Stiles looks at the camera and remembers where he’s at, what he’s doing. Fuck. He needs to get his head back in the game. “Dare? Cause you’re daring to hire me tonight? Cause you’re a daring kinda guy? Dare. I like it.”

“Just open the box, Scott.” The dude really needs to get laid if he’s this uptight during a camshow. Stiles also hopes that he doesn’t use his name that often because nothing throws him out of a scene faster than hearing someone moaning Scott’s name. In hindsight, he shouldn’t have used his best friend’s name for a camshow, but Stiles had originally wanted something he’d remember and not ignore if someone said it.

“I enjoy getting presents from strange men,” Stiles says, winking at the camera before he pulls the end of the shipping tape and rips it off. He opens the box and eagerly looks inside.

“Good to know, Scarlett.”

At that, Stiles grins at the camera. “Dude, you know Clue? Best movie ever. Your cool points just went up for that reference, Dare. I could detect the sarcasm even with the computerized voice, which is awesome.”

“Finish opening your present. It’s, uh, what I want tonight. If you’re willing and able.”

“Willing and able?” Stiles arches a brow at that before he gets back to opening the box. When he sees what’s inside, he whistles. It’s a knotted dildo, not as long as his own dick but definitely thicker. He’s never actually used a knotted toy before, but he’s getting hard just thinking about it.

“I want to watch you fuck yourself on it. Want to watch you take the knot while fucking your hand. Want you to show me your ass after, when it’s gaping.”

Stiles licks his lips and slowly nods. “I can do that. To take something that thick, I’ll have to prepare myself, though.”

“I know. I want to watch.”

“Okay, Dare.” He grabs the bottle of lube and gets on his knees, ass facing the camera. He starts fingering his hole, loosening himself up for the dildo. “You like to watch, huh?”

“I’d rather be there with my fingers in your ass.” There’s a pause, long enough that Stiles looks at the computer in concern, wondering if they got disconnected. Then the typing starts again. “I love how your hole just sucks in your fingers. So desperate to be filled, like it can’t stand being empty. You should add another.”

“Is that all you’d want in my ass if you were here?” Stiles teases, starting to profile Dare. Probably repressed, into some kinky stuff considering the knotted toy, definitely not used to being so open about what he wants judging by the pauses and somewhat awkward flow of dirty talk. He’s paying Stiles to live out a fantasy, so it’s up to him to make sure Dare gets his money’s worth. “Bet you’ve got a lot of ideas how to fill my ass, don’t you, Dare?”

“Yes, I do.”

“Why don’t you tell me about them while I get my ass nice and loose for my pretty present?” Stiles is a talker, but he can’t really hold the entire show if he doesn’t get _something_ from his client that lets him know what direction to go. “Can you see clearly?”

“I’m not much of a talker. You can talk. I like it when you talk. And, yes, I can see everything.”

“Alright. I can talk.” Stiles squirts a little more lube on his fingers before he eases them into his hole. He’s got two in right now, but he adds a third, fucking himself slow and easy. “You like that, Dare? Like seeing me stretch around three fingers? I like it. Feels good. Not as good as your fingers would feel, though. It gets lonely sometimes, only fucking myself.”

“There’s no way someone like you would be alone long if you were interested in finding a partner.” Dare’s words make Stiles laugh softly.

“Someone like me, huh? You mean a camboy who likes playing with his ass? Actually, that can be a problem because I like my show, and a partner might not understand that.” Stiles looks right at the camera as he eases in a fourth finger. He bites his lip at the stretch, eyelashes fluttering as he takes a few steady breaths. “I’ll tell you a secret, Dare. I might love having my hole full, but I prefer doing the fucking when it comes to off-camera play.”

“I know.”

Stiles blinks at that, honestly a bit surprised by the straightforward comment. He’s versatile, but his show tends to focus on his ass, so he figures most of his viewers think of him as some needy bottom boy. Hell, he _knows_ a lot of them do based on their comments in his room. They aren’t shy about making their opinions known, after all. “What do you mean? How do you know?”

“It’s obvious to anyone who is really paying close attention to you.” Dare’s cursor blinks for several seconds before it begins moving again. “There’s an intensity you get when you’re using that fleshlight, and you only come when you’re jerking yourself off.”

“Now, Dare, that’s pretty circumstantial evidence to confirm I like giving more than receiving when it comes to fucking.” Stiles twists his wrist, groaning as the change in angle lets him stroke his prostate. “And it’s stereotyping, isn’t it? Not many guys I know can get off just from being fucked, not without some direct stimulation.”

“I can.”

“Yeah? You like getting fucked, Dare?” That’s definitely not something Stiles is told often by one of his clients. They’re paying for the fantasy of fucking him, after all. Not that most of his shows, if any, go exactly like this one is going. Dare isn’t responding the way a normal client does, and that’s odd, especially when coupled with the fact that the guy sent him an expensive knotted dildo for this show.

“I’m versatile, but I have my preferences.”

“Touche.” Stiles can’t help but grin at the camera. “How do I look? Am I ready for your present yet?”

“You’re ready. You like it when there’s a bit of sting.”

“You’ve watched me closely, haven’t you?” Stiles’ dick likes the idea that this guy is so into him that he’s noticed subtle stuff that not even his long-term regulars notice. He _does_ like it when there’s a little pain during penetration because he enjoys that stretch, feeling it thrusting inside him. He never loosens himself as much as he loosens his partners for his own dick.

“All the time.” There’s a pause when Stiles gets the dildo and strokes his fingers over it, making sure to touch every bump and vein in the silicone. “I really like watching you.”

“That’s good, Dare. Because I _love_ being watched by you.” Stiles brings the toy to his mouth, rubbing the head against his lips. “Do you want me to suck your present before I fuck myself on it? Want to see if I can take the knot orally?”

“Please.”

Instead of replying, Stiles licks the underside of the toy, making a show of it. He begins sucking on the toy, his mouth stretched wide, lips probably look obscene as he bobs his head up and down, slurping and making noises loud enough for Dare to hear over their connection. There’s no words at all coming from the computer, which means Dare is probably enjoying the show. Maybe he’s touching himself.

The vision of Derek Hale jerking himself off while watching Stiles suck the dildo flashes through his mind, and he moans, reaching down to squeeze his dick. Derek Hale on his knees begging for Stiles’ dick is a common fantasy the past few months, but Stiles is now thinking about using this toy on him, fucking him until he’s a writhing mess of emotions, needy and desperate.

He can feel the toy in his throat now, his mouth stretching to try to take in the knot. There’s a moment where he feels like he’s choking, something he hasn’t experienced unintentionally since he first trained himself to deepthroat, but he doesn’t panic. Instead, he keeps sucking, and the moment passes. He’s soon got his teeth around the knot, and he feels pretty damn accomplished.

“You took it. Wish you could see yourself. I can see it in your throat.”

The computerized voice is not sexy at all, but imagining the words being said in Derek Hale’s surprisingly soft voice _is_. Stiles sucks on the dildo for a few more minutes, but he’s loose and ready to feel this bad boy in his ass, so he doesn’t tease for too long. When he pulls it out of his mouth, he takes a few ragged breaths before grinning at the camera. “Guess I’ll have to watch a playback of this vid later, since it got you so hot, Dare.”

“How much for a copy?”

“You’re not recording it?” Stiles strokes his fingers over the wet toy and smiles. “Most people seem to do that even if they probably shouldn’t. I don’t care, so long as it’s not posted anywhere. I’ll tell you what. Since you sent me such an enjoyable new present, I’ll give you a copy for free. But don’t tell anyone.”

“I can pay.”

“Shh, Dare. It’ll be our little secret, alright? Another one we’ll share.” Stiles winks before he picks up the bottle of lube and lathers the dildo. “Now, I hope you’re ready to see me take this knot because my ass is aching for it.”

“I’ve been ready for over a year.”

“That long, huh?” Stiles knows the names who visit his room, and Lobo just showed up a few weeks ago. Maybe he used a different name before that? There are only a few that Stiles has ever blocked, fortunately, and Dare isn’t any of those unless he’s had a personality transplant since getting blocked. “Well, you know what they: good things come to those who wait.”

“My sister always tells me that patience is a virtue. I prefer your take on the cliché.”

“That’s because I’m awesome and always right.” Stiles moves on his bed, turning around so his back is to the camera. It’ll give Dare the best view of him fucking the toy.

“No. Turn around. I want to see your face. And your cock.”

“Thought you were paying to see me fuck this magnificent toy?” Stiles is caught by surprise, since he’s never had a client want to see his face instead of his ass. He feels a bit disconcerted but quickly recovers. “You sure about that, Dare? Don’t you want to see my tight hole suck in this thick toy?”

“I want to watch your face as you take the knot. Don’t care about your ass. Not right now.”

“I have to tell you, that’s the first time I’ve ever heard that statement during the four years I’ve done this show,” he admits, changing positions again. “People pay to watch me because of my ass, you know?”

“I know. It’s a great ass, if you’re into that. I’d rather ride your huge cock while you’re fucking yourself on that toy, though.”

“Damn it, Dare. You can’t just say things like that without warning. The computer voice isn’t sexy, no JARVIS for me, sadly, but those words nearly made me shoot off,” he mutters, not that he mentions that it’s because he had a flash of Derek Hale riding him like that when he heard Dare’s words.

“Sorry.”

“No, you’re not.” Stiles shakes a finger at the camera. “Don’t think I’m not onto you, Dare. You like throwing me off-guard and surprising me. I’ve figured you out.”

“Sure you have.” It’s obvious that Dare is being a sarcastic ass, which shouldn’t turn Stiles on but totally does. “If you don’t start fucking soon, the lube will dry out.”

“Right. Got it. Back to business.” The lube is still fine, but he does check because he got distracted. He really is glad that Dare isn’t as uptight as some clients. Tonight’s show has been a bit of a mess and all over the place, not that that’s just Stiles’ fault, but he still feels a sense of professionalism failure at the moment.

His ass is still loose, but not quite enough to take the thick toy without that burning stretch that he kinda loves. He bites his lip as he begins moving up and down on the toy, taking it slow, inch by inch. The computer is silent as Dare focuses on what he’s paid for, which is watching Stiles fucking himself on a knotted dildo. Now that he’s started, he focuses on the act itself. He makes noises, not faking them but maybe being a little louder due to the camera, and he jerks his dick as he bounces up and down.

There’re a couple of times that he loses his grip on the toy, having to shift and lose the moment briefly, but he quickly gets his pace back up. When he’s riding it easily all the way to the knot, he looks at the camera and smiles, a lazy sexy twist of lips that he figures is a bit dazed because, man, this toy is pretty damn awesome. “Gonna take the knot now, Dare. Gonna take your knot and come so hard.”

The stretch of the knot against his rim makes him grit his teeth. It’s almost too much, but he likes a challenge. He lets go of his dick to reach back to balance on the bed, shifting a bit and rolling his hips. The noises he’s making now aren’t exaggerated. His lips are caught between his teeth, his eyes half-closed, and he can feel sweat trickling between his shoulderblades as he pushes—pushes—pushes—and _finally_ gets the knot past his rim.

“Oh fuck.” He stops moving, just staying there and adjusting to this large presence in his hole, panting as he reaches up to push his hair back from his sweaty forehead. The knot is rubbing right against his prostate as he begins to move, and he forgets about the camera, forgets about Dare, forgets about everything except coming as he jerks his dick hard while slamming the toy into him as fast and deep as he can manage.

“You’re so fucking gorgeous. So beautiful. Take it. Take it all. Let me watch you come. Damn it, come for me.”

And Stiles does. He comes with a low grunt, back arching, ass clenching tight around the toy, spurt after spurt of seed splashing onto his lower abdomen and the blanket. He falls back on the bed after he comes, breathing deeply, still trembling as he tries to calm down. Eventually, he gets himself under control and ease the toy out of his ass. Remembering Dare’s request, he moves to his knees and shows off his gaping hole to the camera.

“So good. Perfect for me. Knew you would be.”

Stiles sits on the bed and smiles at the camera. “Hope it was as good for you as it was for me, Dare.”

“It was even better.”

“Now, I doubt that. I can’t remember the last time I’ve come that hard.” Stiles runs a hand over his face before he reaches down to wipe the come off his happy trail. He sucks his fingers, looking at the camera from beneath his lowered lashes. “Thanks for the present, Dare.”

“It was my pleasure.”

“I’m sure it was.” Stiles blows a kiss at the camera. “I appreciate your patronage, and I really hope we can do this again sometime.”

“We will.” There’s a notification of a transfer of funds to Stiles’ account, including a five hundred dollar tip. He blinks at the screen of his computer before looking at the camera.

“That’s way too much, Dare. I didn’t even give you a full two hours.”

“It’s not as much as you deserve. You should probably take a shower and try to get some sleep. You’ve got work tomorrow.”

“It’s not that late,” Stiles points out. “And you don’t know if I work or not, so stop being so bossy.”

“I thought you liked bossy. Anyway, I know you’ve got an early meeting tomorrow so stop arguing and do what you’re told. Sweet dreams, Stiles. Thank you for tonight.”

“Night, Dare.”

It’s only after he’s disconnected and turned off the camera that he realizes what Dare said. He freezes in the middle of sliding off the bed, blinking stupidly before he hurries over to his computer and scrolls up to make sure the words typed were what he heard.

They were.

Dare called him _Stiles_. Stiles. Not Scott. And how the hell did the guy know about the meeting tomorrow morning? It was only called this afternoon because Laura and Derek got a new contract signed, and Stiles is going to be on the project team. He knows he didn’t slip up and say anything.

Did he?

Fuck. Maybe he got carried away at some point and blabbed something he shouldn’t? It’s the only thing that makes sense. He’ll have to rewatch his video before sending it to Dare, remove any personal info before sending it, just in case.

Shaking his head, he picks up the toy and heads to the bathroom. “Dumb ass. You know better,” he mutters, annoyed at himself for obviously slipping up. Oh well. He’s slipped before, and nothing’s come of it, so he’ll just hope this Dare guy is some dirty old man in Alaska or something who has no reason to remember his real name. Right now, he’s got more important things to think about.

Namely, a shower and mentally preparing himself to deal with Derek Hale tomorrow for a two hour meeting without making a fool of himself with flailing and talking too much and saying inappropriate things. Or with getting distracted with dirty fantasies when he needs to be paying attention to work stuff.

No, it’ll be both.

It’s _always_ both when it comes Derek fucking Hale, and his judgy eyebrows and sexy frown and glowering attitude that is only focused on Stiles because he dared call the guy dude when they first met. And, okay, maybe, just maybe, it’s also because he blurted out that he’d like to climb him like a tree _before_ he knew that he was Derek Hale. It was a compliment! Not that it seemed to have been taken that way.

Instead, Derek Hale only spoke to Stiles when forced, and he loomed around everywhere silently judging him. It wouldn’t be that bad except for the fact that Stiles also became the go to IT guy for major projects, which means he can’t avoid Derek Hale as much as he’d like.

Case in point: tomorrow’s meeting. Derek Hale in his expensive suit watching him across the boardroom table for hours is inevitable. And, after tonight’s session, Stiles is going to have a hard time _not_ thinking about fucking him hard while riding a knotted dildo. He needs to make a mental note to not schedule anymore private shows the night before a meeting, obviously.

But he’ll make it through the meeting fine, like always. Laura thinks he’s adorable and charming, exact quote, and the rest of the team totally values him even if Derek Hale doesn’t. After the meeting, he’ll probably come home and have a little one on one time with his new toy and his fist while thinking about Derek Hale in that sexy suit, but no one needs to know about that.

Stiles knows how to keep a secret, after all.

**Author's Note:**

> [Tumblr](http://inell.tumblr.com)


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